Trifluoroacetic acid → Trifluoroacetic acid

HRID 1944582Notes

Reaction equation

HRID 1944582 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8](C2C=CC=CC=2)[C@@:9]([NH:38]C(=O)OC(C)(C)C)([C:11]2[O:12][C:13]([C:16]3[CH:21]=[C:20]([N:22]([CH3:27])[S:23]([CH3:26])(=[O:25])=[O:24])[N:19]=[C:18]([N:28]([CH2:34][CH2:35][O:36][CH3:37])[CH2:29][C@@H:30]4[CH2:32][C@H:31]4[CH3:33])[CH:17]=3)=[N:14][N:15]=2)[CH3:10])=[CH:4][CH:3]=1.[C:52]([OH:58])([C:54]([F:57])([F:56])[F:55])=[O:53]>C(Cl)Cl>[NH2:38][C@:9]([C:11]1[O:12][C:13]([C:16]2[CH:17]=[C:18]([N:28]([CH2:34][CH2:35][O:36][CH3:37])[CH2:29][C@@H:30]3[CH2:32][C@H:31]3[CH3:33])[N:19]=[C:20]([N:22]([CH3:27])[S:23]([CH3:26])(=[O:24])=[O:25])[CH:21]=2)=[N:14][N:15]=1)([CH3:10])[CH2:8][C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1.[C:52]([OH:58])([C:54]([F:57])([F:56])[F:55])=[O:53]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86616992HCID 86616992, compound

Product 2

HCID 6422Trifluoroacetic acidHCID 69519419HCID 69519419, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl [(1R)-2-(4-fluorophenyl)-1-(5-{2-{(2-methoxyethyl)[(trans-2-methylcyclopropyl)methyl]amino}-6-[methyl(methylsulfonyl)amino]pyridin-4-yl}-1,3,4-oxadiazol-2-yl)-1-methyl-2-phenylethyl]carbamate (11.58 g, 17.9 mmol) in DCM (75 mL) cooled to 0° C. was added TFA (25 mL) and the reaction mixture was stirred at rt for 16 h, concentrated in vacuo, and reconcentrated several times from DCM, to give N-(4-{5-[(1R)-1-amino-2-(4-fluorophenyl)-1-methylethyl]-1,3,4-oxadiazol-2-yl}-6-{(2-methoxyethyl)[(trans-2-methylcyclopropyl)methyl]amino}pyridin-2-yl)-N-methylmethanesulfonamide as a TFA salt. MS M+1=547. 1H NMR (400 MHz, CD3OD) δ 7.10 (m, 5H), 7.01 (s, 1H), 3.82 (t, J=5.86 Hz, 2H), 3.64 (t, J=5.86, 2H), 3.50 (AB overlapping m, 4H), 3.39 (s, 3H), 3.35 (s, 3H), 3.18 (s, 3H), 1.88 (s, 3H), 1.05 (d, J=5.86, 3H), 0.78 (m, 2H), 0.49 (m, 1H), 0.30 (m, 1H).

Workup

  1. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c557b7c053dc4d91a75e247ff37c5b52
Source dataset
uspto-grants-2013_03
Patent number
US08394837B2

Reaction notes

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